An acidic pH independent piperazine–TPE AIEgen as a unique bioprobe for lysosome tracing

Cai, Yuanjing; Chen, Gui; Samedov, Kerim; Su, Huifang; Gu, Xinggui; Li, Shiwu; Luo, Wenwen; Sung, Ho Yung; Lam, Jacky W. Y.; Kwok, Ryan T. K.; Williams, Ian D.; Qin, Anjun; Tang, Ben Zhong

doi:10.1039/c7sc03515b

Cited by 116 publications

(64 citation statements)

References 54 publications

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“…The parent hydrocarbon tetraphenylethylene (1, Figure 1) and numerous substituted derivatives are known to exhibit the phenomenon of aggregation-induced emission (AIE) in which enhanced luminescence is observed upon the restriction of intramolecular bond rotations due to aggregation of tetraarylethylene molecules in solution (e.g., in the presence of poor solvents) or in the solid state [17,18]. This general property of tetraarylethylenes coupled with a geometrically appealing molecular structure has resulted in studies examining the utility of tetraarylethylene derivatives in solution phase and solid state supramolecular assembly processes, often with the aim of capitalizing on enhanced luminescence to deliver new optical or sensing materials [19,20]. Indeed, several crystalline luminescent metal organic frameworks (MOFs) have been prepared using the symmetrical tetraphenylethylene carboxylic acid (2) as well as the extended biphenylethylene analogue (3) as rigid metal ligating components [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35].…”

Section: Introductionmentioning

confidence: 99%

Salts and Co-Crystalline Assemblies of Tetra(4-Pyridyl)Ethylene with Di-Carboxylic Acids

Gabr

Pigge

2018

Crystals

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Tetraarylethylene derivatives are emerging as an increasingly important family of supramolecular building blocks in both solution phase and the solid state. The utility of tetraarylethylenes stems from appealing structural features (rigidity and symmetry) and their propensity to exhibit aggregation induced emission (AIE). In an effort to investigate the luminescent sensing ability of heteroaromatic tetraarylethylenes, we previously prepared tetra(4-pyridyl)ethylene and characterized its solution phase AIE properties. We here report the successful incorporation of tetra(4-pyridyl)ethylene into three distinct salts and co-crystalline assemblies with three organic di-carboxylic acids (oxalic acid, malonic acid, and fumaric acid). Interactions between the tetra(pyridyl)ethylene and di-acid components were found to vary from conventional to charge-assisted hydrogen bonding according to the extent of proton transfer between the acid and pyridine groups. Notably, the formation of pyridinium-carboxylate adducts in the salts does not appear to be strongly correlated with acid pKa. Three distinct network topologies were observed, and all featured the bridging of two or three tetra(pyridyl)ethylene groups through di-acid linkers. Crystalline assemblies also retained the AIE activity of tetra(pyridyl)ethylene and were luminescent under UV light. As tetra(4-pyridyl)ethylene features four Lewis basic and potentially metal ligating pyridine rings in a relatively well-defined geometry, this compound represents an attractive building block for the design of additional crystalline organic and metal-organic functional materials.

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Section: Introductionmentioning

confidence: 99%

Salts and Co-Crystalline Assemblies of Tetra(4-Pyridyl)Ethylene with Di-Carboxylic Acids

Gabr

Pigge

2018

Crystals

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“…In addition bioimaging application requires transformation of as synthesized nanoparticle to nanoprobe that is yet to be achieved for many cases. Aggregation induced emission active molecular probes are emerging as another alternative of molecular probes that can avoid photobleaching and fluorescence quenching issues (Cai et al, ; Mei et al, ; Qian & Tang, ).…”

Section: Introductionmentioning

confidence: 99%

Fluorescent carbon dots as intracellular imaging probes

Ali

Ghosh

Jana

2020

WIREs Nanomed Nanobiotechnol

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Fluorescent carbon dot has emerged as promising alternative of conventionally known quantum dot or molecular probe as potential intracellular imaging probe. In particular, <10 nm size, tunable and bright fluorescence of carbon dot deserve the application potential as intracellular imaging probe. However, synthesis of carbon dot with narrow particle size distribution, preparation of high‐quality red/near‐infrared emitting carbon dot and appropriate design of functional carbon dot for subcellular targeting are most critical issues. This advanced review focus on the application potential of fluorescent carbon dot as intracellular imaging probe. At first, we briefly discuss different types of fluorescent carbon dots and origin of their fluorescence. Next, we focus on surface chemistry and functionalization which are relevant to intracellular probe development. Finally we have summarized various types of intracellular nanoprobes that are developed from fluorescence carbon dot. This article is categorized under: Diagnostic Tools > in vitro Nanoparticle‐Based Sensing

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“…In recent decades, AIEgens have been proved to possess high photostability, large Stokes shi, excellent capability of longterm tracking and good biocompatibility. [55][56][57][58][59][60][61][62][63][64][65][66][67] Although great attention has been paid to tissue regeneration and lysosome study, 4,5,27,28,[68][69][70] monitoring lysosomal pH during tissue regeneration in vivo has not been investigated yet.…”

Section: Introductionmentioning

confidence: 99%

In vivomonitoring of tissue regeneration using a ratiometric lysosomal AIE probe

et al. 2020

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An acidic pH independent piperazine–TPE AIEgen as a unique bioprobe for lysosome tracing

Abstract: PIP–TPE’s fluorescence turns on blue due to the large viscosity of lysosomes which restricts intramolecular motions but it red-shifts in the bulk.

Cited by 116 publications

References 54 publications

Salts and Co-Crystalline Assemblies of Tetra(4-Pyridyl)Ethylene with Di-Carboxylic Acids

Salts and Co-Crystalline Assemblies of Tetra(4-Pyridyl)Ethylene with Di-Carboxylic Acids

Fluorescent carbon dots as intracellular imaging probes

In vivomonitoring of tissue regeneration using a ratiometric lysosomal AIE probe

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